Holiday houses in Middlesex County

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Top-rated holiday rentals in Middlesex County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Home in Old Harbour
4.84 out of 5 average rating, 25 reviews

Cool Cozy Cottage II. 2 bedroom oasis Free parking

This beautiful 2 bedroom 1 bathroom home is located in the peaceful community of Aviary Old Harbour. Relax in comfort in Queen size bed in the main room with ac comfort. The second room is equipped with two twin beds. 24hrs camera that monitors the entrance. The location gives easy access to the Highway leading to Kingston, Ocho Rios and Montego Bay and also to Mandeville. Enjoy modern amenities with access to wifi and our outdoor verandah. Checkin with through the use of our key box system.

Guest favourite
A spacious bed is presented with soft linens and decorative pillows. Double French doors open to a scenic view of greenery and the ocean. Natural light fills the room, creating a serene atmosphere.
Apartment in Ocho Rios
4.85 out of 5 average rating, 190 reviews

Precious Studio with a Vast Ocean View

We are fully operational post Hurricane Melissa with power, water & wifi Unwind at this stunning ocean-view studio only 5 minutes away from the heart of Ocho Rios. The studio is freshly renovated with granite counter tops in the kitchen and bathroom, and porcelain tile throughout for a luxurious yet homey feel. Enjoy the vast ocean view and dip your toes in the water only a few steps out from the patio. This studio is the perfect place for relaxing, listening to the ocean and enjoying the breeze

Guest favourite
A bright living area is showcased, featuring a comfortable yellow sofa and a wooden coffee table. Large sliding glass doors lead to a balcony with two loungers, providing a clear view of the sea and surrounding greenery.
Condo in Ocho Rios
4.83 out of 5 average rating, 280 reviews

Seafront Apartment nxt to Beach

My place is in Ocho Rios Jamaica , walking distance from Ocho Rios Town centre . Its a homely seafront, split level apartment within a traditional 1960s style past resort directly next to Mahogany beach. Breathtaking sea views, set within a beautiful garden. The people are lovely and the sea and beach/bar are so relaxing. You can book and set sail from the beach on a Cool Runnings catamaran cruise. My place is good for couples, solo adventurers, business travellers, and families (with kids)

Guest favourite
Home in Old Harbour
4.94 out of 5 average rating, 83 reviews

Nicely Furnished-1BR/24hr Sec./AC/Fast Wi-Fi/ NHV4

Come relax a while at this centrally-located place in New Harbour Village. Located on a quiet street this home is clean, comfortable and cozy with a stylish design. Enjoy waking up in a comfy queen-size bed, having a warm rain shower bath, eating your choice of foods and selecting your choices for entertainment. You will be two minutes away from the Old Harbour Town Centre where you can enjoy local foods, shopping and round town travels. What are you waiting for? Come! You will love it here.

Superhost
Condo in Ocho Rios
4.87 out of 5 average rating, 269 reviews

One of Ocho Rios Best Getaway Airbnb!

Welcome to Marazul, a picturesque vacation condo in upscale Columbus Heights, nestled in the hills of Ocho Rios. The perfect gateway with postcard-perfect panoramic ocean views and all the amenities to make your stay feel right at home. Surrounded by beautifully manicured rainforest gardens and with direct access to 1 of 5 community pools. For your convenience, we are centrally located near restaurants, beaches, and the most popular attractions, all within minutes. Do you see yourself here?

Top Guest favourite
A serene outdoor space is showcased, featuring a shaded gazebo surrounded by palm trees and manicured greenery. In the background, a swimming pool is visible, with residential buildings partially framed by the lush hillside.
Condo in Ocho Rios
4.93 out of 5 average rating, 122 reviews

The Ocean Ridge - Ocho Rios, Stunning Sea Views

The Ocean Ridge Apartment (K1), Sky Castles, Columbus Heights, in Ocho Rios. With jaw-dropping views of the sea & cruise ships, this renovated studio apartment is ideally located for a relaxing getaway or a longer remote working vacation. The unit is bright & uncluttered with a tastefully modern décor. K1 is located in a gated hillside community, close to all major attractions, some walkable. The area provides unparalleled scenic views of the sea, mountains & flora of a tropical paradise.

Guest favourite
A modern kitchen is showcased with sleek white cabinetry and a stainless steel gas range. A mosaic backsplash complements the area. Natural light filters through the window, while a vibrant yellow curtain adds a pop of color. Stainless steel appliances are also present.
Apartment in Portmore
4.87 out of 5 average rating, 60 reviews

"Phoenix Tranquility"

Indulge in the welcoming atmosphere of our intimate retreat – an enchanting 1-bedroom, 1-bathroom Airbnb, your ideal home away from home for your upcoming getaway. Tucked away in the vibrant heart of Portmore at Phoenix Park Village, this meticulously designed and stylish space offers all the necessities for a cozy and memorable stay. Conveniently located, it's just a 10-minute drive from the renowned Sovereign Village Portmore and a mere 15-minute drive from the famous Hellshire Beach.

Top Guest favourite
A comfortable living area features a spacious sectional sofa, complemented by a coffee table and inviting decorative accents. Bright artwork depicting beach scenes adorns the wall, while a dining table with chairs is positioned nearby, enhancing the functional layout of the open space.
Home in Old Harbour
4.95 out of 5 average rating, 22 reviews

Camerons Cove-378 Home in Whim Estates Old Harbour

A cozy and well-appointed space designed for comfort and relaxation in a gated and secured community. Located in a convenient and desirable area, you’ll love the warm and welcoming atmosphere, perfect for families, couples, or solo travelers. What makes it so special is the thoughtful amenities, stylish decor, and personalized touches that make you feel right at home. Whether you’re looking for a peaceful retreat or easy access to local attractions, we offer you an unforgettable stay.

Guest favourite
Condo in Ocho Rios
5 out of 5 average rating, 5 reviews

Villa Topenga Luxury 1 Bedroom - East

Discover the ultimate getaway at Villa Topenga, nestled in the serene Crystal Shores Resort, Rio Nuevo, near Ocho Rios, Jamaica. This exquisite villa offers a spacious bedroom with en-suite bathroom. Enjoy the convenience of essential amenities, including air conditioning, high-speed wireless internet, a fully equipped kitchen with a stove and refrigerator, and more. Immerse yourself in the beauty of Jamaica while enjoying the comforts of home.

Guest favourite
A two-story blue building is showcased, featuring multiple entrances and a balcony with black railings. The exterior is accented by white trim and several windows. A paved pathway leads to the entrance, bordered by a small garden with a young tree.
Apartment in May Pen
4.89 out of 5 average rating, 47 reviews

Home

Kick back and relax in this calm, stylish space. Home is centrally located in a gated secure premises in May Pen, Clarendon. It is 2 mins from the nearest hospital. Doctors offices, restaurants, shopping, spas, salons, etc. Attractions in Clarendon includes, the Milk River Mineral bath, Farquahar beach, salt River mineral spring and other hidden gems. Home is also 2 mins away from the high way 2000.

Top Guest favourite
A fully refurbished cut stone cottage sits amidst lush tropical greenery, featuring a shaded verandah adorned with colorful cushions. Stone walls complement the natural surroundings, while palm trees and vibrant foliage create a serene retreat atmosphere.
Cottage in Ocho Rios
4.99 out of 5 average rating, 533 reviews

"Tumbleweed Cottage"

Quick update after hurricane Melissa… We are back up and running with no structural damage🙏. We have been hosting guests. Power is back, water is flower and Starlink is providing Internet. 😁🙏 Quiet very private one bedroom fully refurbished cut stone cottage with your own pool. Located less than a mile from Upton (Sandals) Golf Course. Ideal for Golfers, Writers, Painters and Weekend Travelers.

Top Guest favourite
Home in Spanish Town
4.96 out of 5 average rating, 76 reviews

Studio Serenity

Modern, peaceful studio in Angels Grove, perfect for your Jamaican getaway. Minutes from restaurants and the Knutsford Express depot. Easy toll road access to north coast attractions. Equipped with WiFi, AC, and kitchenette. Ideal for solo travelers, couples, or business trips. Your serene home base for island exploration.

Popular amenities for Middlesex County holiday rentals